Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond - Université de Lorraine Access content directly
Journal Articles Tetrahedron Year : 2014

Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

Abstract

delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)-delta-azaPro bond when delta-azaPro is protected by a Boc group. The removal of the Boc protection leads to the establishment of a C-10 pseudocycle via a hydrogen bond network favoring the cis conformation of the Xaa(1)-delta-azaPro bond.
No file

Dates and versions

hal-01498198 , version 1 (29-03-2017)

Identifiers

Cite

Emelyne Humbert-Voss, Axelle Arrault, Brigitte Jamart-Grégoire. Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond. Tetrahedron, 2014, 70 (2), pp.363-370. ⟨10.1016/j.tet.2013.11.049⟩. ⟨hal-01498198⟩
73 View
0 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More